Acetic Acid → HCID 3069943, compound

HRID 1763067Notes

Reaction equation

HRID 1763067 reaction equation
Cl[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=1)=[O:4].[BH4-].[Na+].C(O)(=O)C.[C:18]([NH2:22])([CH3:21])([CH3:20])[CH3:19]>CO>[F:11][C:8]1[CH:9]=[CH:10][C:5]([CH:3]([OH:4])[CH2:2][NH:22][C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6385Tert-ButylamineHCID 1202482-Chloro-4'-fluoroacetophenoneHCID 4311764Sodium borohydride

Product 1

HCID 3069943HCID 3069943, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
-5 °C

Procedure

50 g (0.289 mol) of α-chloro-p-fluoroacetophenone are dissolved in 900 ml of methanol. The mixture is cooled to -5° C. and 5.80 g of NaBH4 are added. It is left in contact for 1 hour then 10 ml of acetic acid are added. 151 ml of tertiarybutylamine are added and the mixture is refluxed for 12 hours. It is evaporated to dryness and the residue of evaporation is taken up in distilled water. The free base which has crystallised is filtered off and, by recrystallisation in hexane, 39 g (yield 63%) of 1-(4-fluorophenyl)-2-tertiarybutylamino-1-ethanol are obtained. m.p. 117° C.

Workup

  1. temperaturethe mixture is refluxed for 12 hours
  2. customIt is evaporated to dryness
  3. customthe residue of evaporation
  4. customThe free base which has crystallised
  5. filtrationis filtered off and, by recrystallisation in hexane

Sources & evidence

ORD record
ord-4e45208013e94df094335c8a456cfaf4
Source dataset
uspto-grants-1989_05
Patent number
US04835315

Reaction notes

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